Synthesis of Stereodefined 3,4-Disubstituted Piperidines through Rearrangement of 2-(2-Bromo-1,1-dimethylethyl)azetidines | Zendy

Matthias D’hooghe | Zendy; Norbert De Kimpe | Zendy; Karen Mollet | Zendy; Leen Broeckx | Zendy

Open Access

Synthesis of Stereodefined 3,4-Disubstituted Piperidines through Rearrangement of 2-(2-Bromo-1,1-dimethylethyl)azetidines

Author(s) -

Matthias D’hooghe,

Norbert De Kimpe,

Karen Mollet,

Leen Broeckx

Publication year - 2011

Publication title -

heterocycles

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.242

H-Index - 64

eISSN - 1881-0942

pISSN - 0385-5414

DOI - 10.3987/com-11-s(p)3

Subject(s) - chemistry , nucleophile , bicyclic molecule , ring (chemistry) , lactam , stereochemistry , medicinal chemistry , organic chemistry , catalysis

cis-2-(2-Bromo-1,1-dimethylethyl)azetidines, synthesized by monochloroalane reduction of the corresponding beta-lactams, were shown to be excellent building blocks for the synthesis of stereodefined 4-bromo-, 4-fluoro-, 4-acetoxy- and 4-hydroxypiperidines in DMSO. During these transformations, the initially formed bicyclic azetidinium intermediates underwent ring opening by a variety of nucleophiles

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